Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
  • C08G63/08—Lactones or lactides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/85—Polyesters
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
  • A61L31/04—Macromolecular materials
  • A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Definitions

• the invention relates to absorbable, physiologically acceptable copolymers and their use.
• DE-OS 36 20 685 agents based on free-flowing to solid oligomeric esters of lactic acid and / or glycolic acid for covering undamaged and / or injured human or animal skin are known. These preparations essentially consist of the oligomeric esters as a resorbable carrier or film images and can additionally contain substances that care for the skin, regenerate, disinfect or stimulate the epithelium.
• FR-OS 21 26 270 also discloses film-forming polymers of lactic acid and glycolic acid in solvents such as, for example, ethyl acetate, which additionally contain pharmacological active ingredients and can be used, for example, as a spray dressing.
• copolymers of lactide and ⁇ -caprolactone are known from US Pat. No. 4,045,418 or 4,148,871, which are physiologically are harmless and can be used, for example, as subdermally implantable containers for pharmaceuticals.
• the compatibility and the biodegradability of such containers is described, for example, in the Journal of Biomedical Materials Research, Volume 13, pages 497 to 507, 1979 and in Naltrexone: Research Monograph 28, National Institute on Drug Abbusus, 1983 by the working group Colin G. Pitt et al. reports.
• a disadvantage of the previously known mono- and copolymers of lactic acid and glycolic acid is the fact that they are compounds which are usually applied in solutions and which are inherently relatively hard and not very flexible, so that such sprayed-on films after the evaporation of the solvent quickly becomes brittle and cracked, in addition to which the adhesion to the skin or wound area is not particularly good.
• the previously used polymers of lactide and ⁇ -caprolactone are generally rigid thermoplastics, which are suitable, for example, for the production of containers, but were not suitable for topical use.
• copolymers of racemic lactide and ⁇ -caprolactone, ⁇ -valerolactone, racemic ⁇ -decalactone or ⁇ -hydroxybutyric acid is now proposed, the copolymers being converted from about 95 to 70 to 5 to 30 by reacting the monomers in a molar ratio of lactide to reactant with the addition of known metal carboxylates as initiators at temperatures of about 150 ° C for a period of about 16 to 48 hours.
• the copolymers according to the invention are to be viewed in chain length as poly- and oligomers and are a mixture of mono-, oligo- and polymers in front. They are colorless, transparent compounds which, depending on the molar ratio of the monomer components, are viscous to rigid.
• the claimed compounds are produced by reacting the monomers in a molar ratio of lactide to reactant of about 95 to 70 to 5 to 30, the increase in the lactide content leading to an increase in a softening temperature. The reaction takes place with the addition of metal carboxylates known per se as initiators at temperatures around 150 ° C. for a period of about 16 to 48 hours.
• the ratio of reaction mixture to initiator is about 100 to 1 to 500 to 1, increasing this ratio in the reaction increases the proportion of longer molecular chains and thereby also increases the softening point is conditional.
• Tin-II-diethylhexanoate is preferably used as the initiator, since it has been found that other initiators known per se generally give a lower yield or lead to clouding / coloring.
• a temperature of 150 ° C. and a reaction time of 16 to 48 hours should not be exceeded, since the polymer may already start to degrade if it is heated for too long. After the desired reaction time, the reaction is stopped either by cooling the reaction mixture or by adding, for example, chelating agents.
• the reaction mass is generally precipitated with 600 to 800 times the amount of alcohol; if necessary, the reaction mass can also be washed out with water or an aqueous solution, since this also allows a large part of monomers, short-chain oligomers or plasticizers to be removed.
• plasticizers can be added to the reaction mass to change the softening temperature and diffusibility. Excess caprolactone, tributyl citrate or phthalic acid ester are preferably used as plasticizers. The proportion of plasticizers should generally not exceed 10 to 20% by weight.
• copolymers according to the invention can be dissolved in suitable organic solvents such as, for example, ethyl acetate, acetone, methylene chloride or THF. They can be rolled out into foils without any additional additives, but they can also be produced by evaporation, for example. Other processing methods suitable for plastics can also be used.
• suitable organic solvents such as, for example, ethyl acetate, acetone, methylene chloride or THF.
• Both the monomers and the polymers are in vivo and degraded in vitro by hydrolysis.
• the copolymers and their breakdown products are medically harmless and not allergenic.
• the monomers are further metabolized in vivo via the citric acid cycle or via the fatty acid metabolism. It has been found that the higher the lactide content, the shorter the times for hydrolytic degradation.
• the polymers claimed according to the invention can be used for a variety of medical and cosmetic purposes.
• a main area of application is the use as a surgical incision film.
• the compounds present in solution in a suitable solvent such as methylene chloride, acetone or ethyl acetate can easily be mixed with known disinfectants; a combination with local anesthetics is also possible.
• a disinfectant effect is already given due to this solvent.
• copolymers with a molar ratio between 70 to 30 to 85 to 15 and a reactant to initiator ratio of about 300 to 1 to 500 to 1 and a polymerization time of 24 hours. These are washed copolymers; but unwashed copolymers with molar ratios between 80 to 20 to 90 to 10 and a ratio of reactant to initiator of 100 to 1 to 400 to 1 with the same polymerization time can also be used well.
• the agents according to the invention can be used particularly advantageously as a liquid glove when dealing with allergens.
• they are also a real alternative for allergy sufferers with detergent or detergent allergies. Due to the long durability and the good adhesion, such solutions can also be used as an aid in camouflage and especially in combination with sun protection factors as long-lasting sun protection, which makes re-application after swimming unnecessary for days, for example.
• copolymers of lactide and the other lactones such as valerolactone, heptalactone, decalactone or else of ⁇ -hydroxy acids such as ⁇ -hydroxybutyric acid can also be prepared in a corresponding manner and taking the molar ratios into account.
• D, L-lactide and ⁇ -caprolactone are slowly heated to 150 ° C. in a molar ratio of 90 to 10 corresponding to 73.5 grams to 6.5 grams.
• the mass is then heated in an oil bath at 150 ° C. for 24 hours.
• the mass is then cooled and can be made up to 1 liter with ethyl acetate at 70 ° C. and treated on a shaker for 36 hours.
• the finished solution can then be used directly as a liquid spray.
• the correspondingly prepared solutions can be used for use as a sun protection spray or as a make-up base.
• the known solution is mixed with the usual UVA and UVB filters.
• the solution prepared according to Example 1 is filled into pump sprays or aerosol sprays known per se.

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• General Health & Medical Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• Epidemiology (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Birds (AREA)
• Organic Chemistry (AREA)
• Polymers & Plastics (AREA)
• Medicinal Chemistry (AREA)
• Heart & Thoracic Surgery (AREA)
• Surgery (AREA)
• Vascular Medicine (AREA)
• Dermatology (AREA)
• Polyesters Or Polycarbonates (AREA)
• Materials For Medical Uses (AREA)

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• 1992
  • 1992-02-11 EP EP19920102237 patent/EP0509203A3/de not_active Ceased

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